Hydrochloric Acid → Suprofen

HRID 461714Notes

Reaction equation

HRID 461714 reaction equation
CC(N)C1C=CC=CC=1.[C:10]1([C:15]([C:17]2[CH:27]=[CH:26][C:20]([CH:21]([CH3:25])[C:22]([OH:24])=[O:23])=[CH:19][CH:18]=2)=[O:16])[S:14][CH:13]=[CH:12][CH:11]=1.Cl>O>[C:10]1([C:15]([C:17]2[CH:27]=[CH:26][C:20]([CH:21]([CH3:25])[C:22]([OH:24])=[O:23])=[CH:19][CH:18]=2)=[O:16])[S:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70638167(+)-p-(2-Thenoyl)hydratropic acid alpha-methylbenzylamine

Product 1

HCID 5359Suprofen

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.5 Parts of (-)-p-(2-thenoyl)hydratropic acid α-methylbenzylamine are suspended in water and acidified with hydrochloric acid. The product is extracted with ether. The organic layer is washed with water, dried and evaporated. The oily residue solidifies on triturating in petroleumether. The solidified product is filtered off and dried in vacuo at 50° C, yielding (+)-p-(2-thenoyl)hydratropic acid; [α](1% in MeOH) = +44.5°.

Workup

  1. extractionThe product is extracted with ether
  2. washThe organic layer is washed with water
  3. customdried
  4. customevaporated
  5. customon triturating in petroleumether
  6. filtrationThe solidified product is filtered off
  7. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-87d97368dcc7427dbc766a552a330b81
Source dataset
uspto-grants-1977_12
Patent number
US04064132

Reaction notes

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